Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
5,9-Dihydroxy-4,8,11,11-tetramethyltricyclo[6.3.0.02,4]undecane. Acidcatalyzed Cyclization Product of 6,7-Epoxyhumula-2,9-diene
Misuzu NamikawaTatsushi MuraeTakeyoshi Takahashi
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1978 Volume 51 Issue 12 Pages 3616-3621

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Abstract

6,7-Epoxyhumula-2,9-diene (2) was treated with 1.8 M sulfuric acid–acetone (1 : 1) to yield a new tricyclic diol, 5,9-dihydroxy-4,8,11,11-tetramethyltricyclo[6.3.0.02,4]undecane (9; diol B), together with tricyclohumuladiol (3; diol A), humulenol-II (4), a diol C (5b), a diol D (5a), and an acetonide (8a). The same reaction at 0° gave only 3. Tricyclohumuladiol (3) was shown to be a key intermediate in the reaction of 2 to form 4, 5a, 5b, 8a, and 9.

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